


Awkward

by montecarlogirl87



Category: Supernatural
Genre: M/M, Underage Kissing
Language: English
Status: Completed
Published: 2014-12-15
Updated: 2014-12-15
Packaged: 2018-03-01 16:20:26
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,640
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2779700
Author URL: https://archiveofourown.org/users/montecarlogirl87/pseuds/montecarlogirl87
Summary: <blockquote class="userstuff">
              <p>Sam needs some advice. Unfortunately, Dean’s the only one he trusts.</p>
            </blockquote>





	Awkward

**Author's Note:**

> this was the first wincest, and first slash I ever tried writing...it probably shows lol

An 18 year old Dean laid back on his mattress flipping through the latest issue of Hot Rod. He had his legs crossed and Black Sabbath playing in the background, absentmindedly humming along.  
  
A terrified looking 14 year old Sam burst through his door and shut it again forcefully.  
  
Dean’s eyes glanced over the top of the magazine before once again returning to the current article he was reading about a souped-up Chevelle.  
  
“Dean…I have…problems,” Sam stuttered nervously, wiping his sweaty palms on his jeans.  
  
Dean again looked at him, shrugged, and returned to his reading. “Yeah, I know.”

“Man! Seriously.”  
  
Dean sighed reluctantly and closed the magazine, tossing it to the end of the bed and sitting up. He knew damn well he was the only thing Sam had. Sam was the only thing he had. Living the way they did, constantly moving, constantly changing schools the only real friends they ever had were each other.  
  
“What’s up?”  
  
“There’s this…girl…”  
  
“Really?” Dean asked excited. “I hear those are really rare, I’ve never seen one myself…”  
  
“Shut up!!”  
  
“Alright, alright,” Dean laughed. “What’s goin’ on?”  
  
“She’s a junior…and umm…she asked if I wanted to go to the football game with her tomorrow.”  
  
“Damn, lil freshie Sammy nabbing the older chick, good goin’ bro,” he winked sarcastically.  
  
“Please Dean…I…” Sam sighed.  
  
Dean’s brow furrowed. His lil bro was actually upset about this.  
  
“And…”  
  
“And I’m freaking out! What the hell am I supposed to do?!”  
  
“Go,” he said with a look.  
  
“Dean…I mean…what if…”  
  
“You need a rubber? Dude, you know you can use some of mine…you don’t have to ask.”  
  
Sam hung his head. “No Dean…I…I don’t know what to  _do_ ,” he whispered.  
  
Dean bit the inside of his lip and nodded, finally catching the reason for Sam’s nervousness.  
  
“Alright…” he sighed deep. “Whatya wanna know?”  
  
Sam met his eyes for a second before glancing around the room nervously.  
  
“Dean…I’ve never…I mean…”  
  
“I know you’re a virgin Sam.”  
  
“Not just that…I’ve never even…kissed…before.”  
  
Dean bit his lip. He knew Sammy had been nervous about this kind of stuff but he didn’t think he had been that nervous.  
  
“Alright…well, change that tomorrow.”  
  
Sam rolled his eyes and rubbed his face with his hands.  
  
“Dean…what if I’m not…good…”  
  
“Well, I don’t know what to tell you.”  
  
Sam met his eyes and Dean saw something that made him pause.  
  
“What?” he asked, growing a little concerned.  
  
Sammy again started glancing around the room nervously.  
  
Not a good sign.  
  
“Will you, I mean…would you…teach…”  
  
“No, no, no….Sam that ain’t even cool.”  
  
“Dean…”  
  
“No! That’s…weird.”  
  
“Oh and we’re so normal.”  
  
Dean glared.  
  
“Do I need to remind you you’re the one who taught me how to…” Sam sarcastically said accompanied with a jacking motion of his hand.  
  
It was Dean this time that glanced around the room. That had been weird…being the one to, basically teach Sam how to accomplish…things.  
  
“Come on Dean…this is nothing compared to  _that._ ”  
  
“It’s weird.”  
  
Sam just gave a look.  
  
 _Shit._  
  
Dean got up and paced his small room a second before walking over to the stereo and turning the volume knob up a little before leaning over the dresser.  
  
“Dean…please. I’m seriously freaking right now. And you know you’re the only one I trust. Besides, I don’t even have any friends I could even talk to, let alone be so…blunt with.”  
  
Dean sighed. He knew Sam was right. That’s where that whole ‘how do I’ situation had come up before. They went to each other for the information most kids would gain just hanging with their peers in school.  
  
Only thing is in their life the closest thing to peers they had were the bedraggled hunters that their dad would sometimes come by with.  
  
He licked his lips and turned to face Sam. That was another thing, besides the whole weird thing, they both knew they could trust each other, it was comfortable in a fucked up Winchester kinda way.  
  
“Come here,” he whispered, so low Sam could barely hear it over the music.  
  
Sam swallowed hard, his Adam’s apple bobbing in his throat drawing Dean’s gaze, before shakily taking the steps needed to bring him to his brother.  
  
Dean bit his lip again and shifted nervously, glancing to the floor before rising again to look into Sam’s eyes.  
  
Sam nodded slightly. He knew this was weird, and incredibly awkward.  
  
Dean took one small step forward and placed his hand on Sam’s cheek, his gaze falling slightly to rest on his lips.  
  
He sighed again. And then let out a small huff of a chuckle and shook his head slightly before leaning in to place his lips upon his brother’s.  
  
Sam shook slightly and hesitantly placed his hands on Dean’s stomach, they made contact for the slightest moment before nervously pulling back, just to hover and return to the hard muscled wall again.  
  
Dean’s hand wrapped slightly around his brother’s neck to pull him a little harder into him and increase the pressure on his lips.  
  
 _God this was weird._  
  
He pecked at his brother’s lips over and over, small and enticing before pulling back and running his tongue over his bottom lip while his thumb brushed slowly back and forth against Sam’s cheek.  
  
Sam swallowed again. “Slow…romantic…got it.”  
  
Dean shifted again nervously. Both of them knowing damn well there was more.  
  
“Okay…” he sighed, before leaning in again.  
  
He started with the same small slow kisses, this time Sam matching his ministrations, testing out the new moves.  
  
Dean let the tip of his tongue slip out just slightly to graze Sam’s lips.  _Slow and easy._  
  
Sam froze for a second and dropped his chin, his shaggy bangs brushing against Dean’s forehead, his hand still cupping his brother’s cheek, his other resting lightly on his bony hip.  
  
“You okay?”  
  
Sam nodded. “Yeah.” It was him this time whose gaze fell to Dean’s lips and leaned in slightly.  
  
Dean finished bridging the gap and the kisses continued.  
  
Sam was the first to let his tongue slip ever so slightly through this time. Dean didn’t pull back but waited a second to make sure Sam was okay before letting his follow suit.  
  
And so the kiss progressed, their tongues just barely snaking out to wet each other’s lips. And then they happened to snake out at the same time and stroke quickly against each other.  
  
Sam froze again, but didn’t retreat. Dean didn’t even open his eyes, just stayed still, letting his lips rest lightly against his brother’s, foreheads pushed together. Feeling Sam’s shaky breathing falling on his face he leaned in again and placed another small kiss on him, to which Sam returned somewhat eagerly, increasing the pressure between them and letting his tongue slip out to run along Dean’s lips.  
  
Dean took the hint and let his own slip out lapping once at his brother’s before retreating back into his own mouth. He was almost surprised when Sam’s dared to follow for a split second.  
  
 _Alright now…_  
  
Sam was mid-kiss when Dean thrust his tongue into his mouth a little forcefully. He felt Sam’s hands clench into fists around his black t-shirt and his own fingers dug a little harsher into Sam’s side.  
  
Sam didn’t back away though. He wasn’t sure what to do but tried to match Dean’s ministrations. His tongue caressing his brother’s in his mouth.  
  
Dean withdrew and let Sam follow his lead and take control.  
  
Sam let his own slip out slowly, small advances and retreats until he felt brave enough to delve into his brother’s mouth.  
  
They must have kissed like that for at least five minutes. Advance and retreat. Dean would show him some move, and then give Sam the chance to perform the same thing on him.  
  
 _No wonder the girls like him_ , Sam couldn’t help but think.  
  
Sam had let his hand slowly rise from Dean’s stomach and settled on his pec before reaching around back to grasp at his broad shoulder and pulled him a little closer.  
  
Dean let his own slide lazily behind Sam to rest in the small of his back.  
  
A couple more minutes and the slow cool down on kisses before they were once again back to just lips and no tongue.  
  
When they finally stopped Dean leaned his forehead against Sam’s and sighed.  
  
“You alright?” he asked, his voice a little huskier than was probably normal.  
  
“Yeah,” Sam whispered meeting his brother’s eyes, their arms still wrapped around each other. “Thanks.”  
  
Dean smirked and nodded. “Now you learned from the best so if you don’t score with her that means you’re beyond hope Sammy,” he snarked, slowly drawing himself away from Sam before walking nonchalantly back to his bed and laying back down, returning to the forgotten magazine and flipping it open to the page he had been on.  
  
Sam laughed slightly and ran his hand over his mouth as he shook his head.  
  
“Dean…seriously.”  
  
“I know,” he said solemnly. “You don’t have to explain shit to me Sammy, I know we got a fucked up relationship that brothers probably shouldn’t have…but you know what…that’s life. Neither of us can change it.”  
  
Sam nodded. “I don’t regret it.”  
  
Dean glanced over his magazine. “What?”  
  
“Our relationship. I know we’re one fucked up family…but I know I can trust you, no matter what.”  
  
Dean nodded. “Sam…just shut up…I’ve had enough chick moments for one day,” he said with a grin.  
  
Sam nodded, “Alright, I’m gonna go make dinner, pork chops okay?”  
  
Dean nodded, “Just don’t burn ‘em this time.”  
  
“Shut up,” Sam said with a smile before leaving Dean’s room.


End file.
